A Scalable Membrane Pervaporation Approach for Continuous Flow Olefin Metathesis
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A_Scalable_Membrane_Pervaporation_Approach_for_Continuous_Flow_Olefin_Metathesis.pdf
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Author(s)
Breen, Christopher P.
Parrish, Christine
Shangguan, Ning
Majumdar, Sudip
Murnen, Hannah
Jamison, Timothy F
Bio, Matthew M.
Date Issued
April 2020
Journal
Organic Process Research and Development
Publisher
American Chemical Society (ACS)
Citation
Breen, Christopher P. et al. "A Scalable Membrane Pervaporation Approach for Continuous Flow Olefin Metathesis." Organic Process Research and Development (April 2020): dx.doi.org/10.1021/acs.oprd.0c00061. © 2020 American Chemical Society
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Author's final manuscript
Abstract
The translation of olefin metathesis reactions from the laboratory to process scale has been challenging with traditional batch techniques. In this contribution, we describe a continuous membrane reactor design that selectively permeates the ethylene byproduct from metathetical processes, thereby overcoming the mass-transport limitations that have negatively influenced the efficiency of this transformation in batch vessels. The membrane sheet-in-frame pervaporation module yielded turnover numbers of >7500 in the case of diethyl diallylmalonate ring-closing metathesis. The preparation of more challenging, low-effective-molarity substrates, a cyclooctene and a 14-membered macrocyclic lactone, was also effective. A comparison of optimal membrane reactor conditions to a sealed tubular reactor revealed that the benefits of ethylene removal are most apparent at low reaction concentrations.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/acs.oprd.0c00061
